Made television debut on the series "Kindred: The Embraced"

Cast as young Houdini in the made-for-television movie "Houdini"

Made feature debut in "The Dangerous Lives Of Alter Boys"

Co-starred in the drama feature "The Emperor's Club"

Cast opposite Elisha Cuthbert in the comedy "The Girl Next Door"

Starred as Duncan, a fourteen-year-old misfit farm boy trying to cope with his mother's death in "The Mudge Boy"

Starred with Sigourney Weaver and Jeff Daniels in the family drama "Imaginary Heroes"

Portrayed Jay Adams in the Catherine Hardwicke directed "Lords of Dogtown"; a fictionalized take on a group of skateboarders that originated in Venice, CA during the 1970's

Cast as the infamous drug dealer Jesse James Hollywood, who became one of the youngest men ever on the FBI's most wanted list in Nick Cassavetes' "Alpha Dog"

Portrayed the doomed idealist Christopher McCandless in Sean Penn's adaptation of the 1996 non-fiction book "Into the Wild"; earned a SAG nomination for Outstanding Male Actor in a Leading Role

Played the lead role in the Wachowski brothers' live action film adaptation of the 1960s Japanese series "Speed Racer"

Portrayed activist Cleve Jones in director Gus Van Sant's biopic "Milk"

Played a Vietnam vet in Ang Lee's "Taking Woodstock"